Ciao Christian,
We're glad the forum is of help, it is our pleasure to help out people sort out the information on the web and plan their trip to Tuscany with the best information we can share.
A week trip based in Chianti sounds perfect from which to make day trips around Tuscany.
As far as treatment by other Italians, I don't think your clothes are that important in themselves. Your behavior is more important in general and casual wear is not important if you ask or request things with a smile and appreciative disposition (as opposed to demanding).
You can and should dress casual on vacations, that is what they're for - relaxing and enjoying a new place away from our everyday life routine!
Having said that, I will point out just a few instances where you should consider what you wear.
Churches - more important for women than for men, the main churches in Florence, Pisa and Siena ask that women show respect to the religious site by not showing too much bare skin. This is a problem when it is really hot out and girls and women prefer tank tops or spaghetti strap tank tops and short shorts. Sometimes the church itself will offer a paper poncho for your shoulders so you can enter covered up, othertimes they don't and turn you away. So women should carry a really light shawl or wide scarf in their purses for such occasions. Might not be a problem in September if the weather is mild.
Skirts are always fine for women. Sandals are fine for both sexes, shorts are fine as long as they are at least mid-thigh length for both sexes. Jeans are definitely ok.
Sneakers are fine - you and your family should definitely bring comfortable walking shoes since you'll do a lot of walking as you sightsee.
Eating out - trattorias, osterias and many family restaurants all have casual atmospheres and will not be bothered with what you're wearing. There are a few nicer restaurants where my husband will wear a polo shirt with dark colored jeans to but he never dresses up for eating out. Unless you happen to go to a really fancy restaurant where you would normally dress up in any case, you will find that the majority of even "nicer" restaurants here in Tuscany don't look too closely at how you're dressed as long as you're presentable. Italy is a country of tourism and visitors are always welcome.
Your behaviour and attitude will make the most difference in how you're treated. But just to prepare you, I have to warn you that some Italians don't believe in customer service in general so if you're not treated as you'd expect, the problem isn't that you're a tourist or dressed in a certain way - they treat everyone like that. However, most people in the hospitality industry do show good customer service although we have found many employees of public tourism offices to not be the most helpful sorts.
Hope I've answered your doubts well enough, do let me know if any more questions pop up![]()
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